


Raising Men

by PurveyorOfBadPuns



Series: Dean Winchester, Gender Issues, and Self Esteem [6]
Category: Supernatural
Genre: Abusive John Winchester, Child Abuse, Crossdressing, Gen, Gender Identity, Gender Issues, Genderqueer, Genderqueer Character, Genderqueer Dean Winchester, Homophobia, John Winchester's A+ Parenting, John Winchester's Bad Parenting, Makeup, Paternal Bobby Singer, Teenchesters, Transphobia, Weechesters
Language: English
Status: Completed
Published: 2014-01-16
Updated: 2014-04-22
Packaged: 2018-01-08 23:19:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,241
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1138648
Author URL: https://archiveofourown.org/users/PurveyorOfBadPuns/pseuds/PurveyorOfBadPuns
Summary: <blockquote class="userstuff">
              <p>"John Winchester did not raise his boys to be girls.  He raised them to be men.  So when he walked into the motel room three days early and saw his fifteen year old all dolled up in makeup like– like a fucking fag, he had to admit he kind of lost his shit."</p>
<p>Trigger warning for homophobic language and child abuse (non-graphic).</p>
<p>It takes a village to raise a child, and this is the story of Dean Winchester's village.</p>
            </blockquote>





	1. John

**Author's Note:**

> Flashback time! Any universe where John Winchester goes to heaven is not one I'd like to live in. This is gonna be a two-parter, with the next chapter up in probably less than a week (I'm on a writing kick). I'll add some new tags when the next chapter comes up. (This is the hurt chapter; the next one will be comfort. As my friends say, I love to tear my characters to pieces just to put them back together.)
> 
> This is a lot more angsty than my normal writing, so I'm sorry. It just came out.
> 
> It is not necessary to read the rest in the series to understand this one, but I do suggest it.

John Winchester did not raise his boys to be girls.  He raised them to be men.  So when he walked into the motel room three days early and saw his fifteen year old all dolled up in makeup like– like a fucking fag, he had to admit he kind of lost his shit.

The first thing he saw was the girl, and a bit of pride flared in his chest, because Dean was starting early (even though nothing was happening; their shoulders were shaking like they were laughing at some joke, but they maintained a respectful distance).  Winchester boys got girls, always had.  But then Dean turned around to see who was at the door and John froze, rage boiling in his chest.  This was what Dean did when he wasn't at home?  This kind of thing was what Dean exposed Sammy to?  No wonder Sam kept wanting to grow his hair now.  Before he'd been ready to blame pre-teen rebellion on that one, but now…

Never mind that it was the happiest he'd seen Dean in a long time.

"Get out," he growled at the girl, and she did.  He never once took his eyes off of his son.

"Dad," Dean said, standing as soon as the girl was out the door, mascara-rimmed eyes wide with panic, cheeks pale under a light dusting of blush, and John's stomach caught.

"Where's Sam?" he growled, grabbing Dean's wrist hard enough to make him yelp.  "We're leaving right now."

"He's at after school study group!" Dean said urgently.  "Dad, we didn't think you'd be home for a week!"

"So this is what you do?" John shouted.  "Is this what you get up to the moment I'm out of here?"

"No sir!" Dean answered immediately, and when John saw how valiantly his son was trying to fight back tears, the fighting spirit went right out of him.  He suddenly felt guilty, but reminded himself that he was protecting his son against an even worse evil.  He wouldn't let his kid be one of… those men.  Even if it meant Dean had to hate him in the process.

"Go clean up."  The moment he let Dean's arm go, the kid was gone, slamming the bathroom door behind him.  John thought he heard the bolt click into the lock, and sat down in one of the chairs, rubbing his temples.  In less than five minutes, Dean was out and clean, his face scrubbed to a shiny pink to remove the last vestiges of color.

"Pack up.  We leave in fifteen; got a case a ways from here."

"Yes sir," said Dean, though he refused to look at his father as he started to throw clothes and books in his duffel and Sam's.  That was fine, as long as the message sank in.

\--

Sam threw a fit, of course, he had so many friends, he loved his classes, this school had a decent after school study group, how was he expected to learn if he was always moving around, and it was almost summer, couldn't they just finish out the school year…

"Shut up Sammy," Dean said, and John was surprised when Sam did just that, getting into the car without another complaint.

Maybe he'd been letting Sam spend a bit too much time around Dean.

The first thing he did was pull over at a shady-looking barber and pay him twenty bucks to buzz Sam's hair off.  Sam was sullen for the next couple hundred miles, and Dean wouldn't even look at either of them.

Half an hour outside of South Dakota he called Bobby Singer and asked him to take Dean for a week.

"And Sam?" Bobby asked.

"No, just Dean."

After three weeks, John came back.  Sam greeted Dean enthusiastically, telling him about the new school he went to for a while in Illinois, and did Dean have fun with Uncle Bobby?

Dean smiled and said that he did, but he wanted to hear more about Sam's time at school, so Sam just kept talking.

Even though everything else was mostly the same, John was never able to look at Dean the same way, and Dean seemed to be doing his best to prove that he was a man.  He picked up John's old leather jacket and hadn't taken it off since.  He redoubled his efforts to prove that he was a good hunter, mostly took over care of the Impala and expressed an over the top interest in mechanics.  He swore, he had his first drink of Jack that he tried to pretend didn't make him gag.  He got into cards and gambling, showing off when John was with his hunter buddies.  All the guys thought it was cool, like a trick pony.  They didn't know the truth.

It was almost a relief when Dean got picked up by the cops for stealing.  John wasn't gonna take him back; maybe a boy's home could do a better job of working that out of him, since John was apparently too soft to do the same.

He eventually picked Dean up because he needed him to look after Sammy, he had a case that would have him gone too long to protect the kid himself.  After all, this was the lesser of two evils.

As long as Sammy was safe.


	2. Bobby

**Summary for the Chapter:**

> "'Hey, I tell you about that time I got a free pedicure? At the Mall of America?'
> 
> Dean shook his head, still staring at his knees."

**Notes for the Chapter:**

> If Dean is genderqueer in the show, or at the very least a little metrosexual, I think that Bobby knows. There's that line in Taxi Driver where we find out that Bobby once got (and liked) a pedicure, and Dean was the only one he ever told, and I sort of wanted to explore why. Might do a second section of this later on.
> 
> Also, wahoo! I'm on a posting roll! Might even have chapter 3 up by the end of the week!

Dean was fifteen when he first stayed with Bobby (or anywhere) on his own, without Sam.  John hadn't explained, just dropped the boy off, and he'd been in such a storm-cloud mood, his son looking so shaky that Bobby had just brought Dean inside and fed him a meal, reassured him as best he could without words that whatever this problem was, it was John's, not his.  He asked about the bruises on Dean's wrist, but Dean just clammed up so Bobby put on a cowboy movie and let the subject rest.

"So, kiddo, you wanna tell me what's up?" he questioned casually when the credits started to roll.

Dean shook his head violently, and Bobby sighed.

"Well, Dean, seems to me your daddy's got a bug up his ass 'bout something.  You got any idea about that?"

He was a little surprised when a small sob escaped Dean's throat.

"I didn't mean to, Bobby," he said, and his voice sounded so hopeless that Bobby wanted to blast John Winchester's heart out.

"The hell you think you did, boy?" Bobby asked incredulously.  Dean was pretty much the best kid he knew; guy didn't even smoke.  Sure, he did what he had to to keep Sam safe, but overall he was the most responsible teenager Bobby had ever met.  Probably because he'd been a parent since he was five, said the darker part of Bobby's mind, and probably it was good for him to get some time away from being Sam's bodyguard.  EIther way, he was here now, looking like a kicked puppy.  Why?

Dean was quiet for a long time, long enough that Bobby didn't think he would get an answer, but then Dean spoke.  "I let my… my girlfriend put makeup on me and Dad walked in."

Bobby's chest flooded with relief.  Not that he didn't trust Dean, but his mind was filled with images of drugs and hookers.  Well, now that he thought about it, John might have actually approved of hookers.  "So what?  Lots of kiddos do that.  Don't mean nothing," Bobby said dismissively.

"And I kind of liked it," he admitted, staring straight at his hands.  "I liked how I looked."

"That supposed to shock me, boy?  If your daddy's got a problem with that, it's him who's not a real man."

"You're not gonna tell me to man up or anything?" Dean asked, finally making eye contact with Bobby, who paternally grasped his shoulder.

"Wouldn't dream of it kiddo.  Hell, you've always been a little weird," he said with a smirk.  "And your daddy's way out of line for treatin' you like that."

"He's right, though!" Dean insisted.

Bobby shook his head.  "No, Dean, he ain't.  Your daddy's a lot of things, but right usually ain't one of 'em."

Dean just shook his head and clammed up, so Bobby didn't say anything else, though he gave John his best death glare when he finally came to pick up his son.

\--

Ten years and Bobby didn't hear another mention of it.  He guessed it was a one time deal, or maybe Dean was just better at clamming up than he thought.  It appeared to be the latter when Dean showed up one May after midnight massively drunk on Bobby's front porch.

"Bobby," he slurred, still holding a silver flask

"The hell are you doing, boy?  Get in here," Bobby said, cursorily checking around to see if someone had seen.

"It's wrong, Bobby," he mumbled, following him into the house.

"What's wrong, son?" Bobby asked, firmly steering Dean to the couch.

Dean sat down unsteadily, unscrewing his flask and trying to take a drink before he realized it was empty and cast it aside.  "Me.  Dad.  Everything."

"Now, you gotta be a bit more specific than that," said Bobby, casting a glance around the room to make sure there weren't any open liquor bottles lying around.  He might've been a hypocrite, but he still didn't really approve of Dean drinking.  Half of him still saw Dean as the ten year old who found it such a novelty to go to the park and play catch, not this hulking young man who was, Bobby reminded himself, of legal drinking age.

He still didn't have to like it.

"I like girl clothes, Bobby," Dean groaned, rubbing his eyes with the heels of his palms, and then clarified, "Wearing 'em."

Bobby was a little caught off guard by that admission, but schooled his features, thinking this was probably a bit of a misunderstanding.  "Well, girl stuff's softer anyhow," he said, trying to be reassuring even though he really had no idea what Dean meant.  Did some girl do something?  How did Dean even end up in girls' clothes?  "Hey, I tell you about that time I got a free pedicure?  At the Mall of America?"

Dean shook his head, still staring at his knees.

"Well," Bobby continued, sitting down on the couch next to Dean, "There was a coupon, so I went in to the salon.  Just curious, you know?"  He shifted uncomfortably, but Dean said nothing, so he went on.  "It was pretty damn awesome, actually.  Got a foot massage and everything.  So I said to myself, who the hell cares if it's a 'girl thing'?  I can still enjoy it, right?"  He hoped these were the right words that Dean needed to hear.  He was sure Dean just had his panties in a bunch (excuse the expression) over a girl making him do something and him liking it too much (and he could kill John Winchester for making Dean think he had to get this worked up).

Dean could tell that Bobby had no idea what he really meant, and he wasn't sure if the thought made him relieved or disappointed.  Half of him wanted to tell Bobby everything, about how he didn't always feel like a guy, about how he didn't just like how girl clothes felt, but also how they looked on him.  How he hated how his body looked, all hard muscle, because Dad made him do exercises and run every fucking day.  How he hadn't done them at all since Dad disappeared a few weeks ago.  How disgusting and _wrong_ he felt when he had to look at his own body, how he avoided taking off his clothes except when it was absolutely necessary, and never in front of a mirror except the few times he'd tried on his girlfriends' panties.  How he wasn't _normal_.  But he couldn't say any of that, couldn't risk losing the one person in his life who still seemed to think he was okay, so he held his tongue.

"Now lie your ass down and sleep off all that whiskey, idjit," Bobby said fondly, clapping him on the back, and Dean complied, slowly curling up on the couch that was just a bit too long for him.  Bobby tossed a rough throw blanket over his body and didn't even bother to scold him about putting his boots on the couch.  That could wait.

"I'm not a man," Dean suddenly blurted, half to himself, quietly enough that Bobby almost didn't hear him.

"'Course you are, don't let that daddy of yours tell you otherwise," Bobby scoffed, before turning out the light and heading up to his own bedroom.

Dean just shook his head as he drifted off, not knowing how to tell Bobby that this wasn't something that came from his father or anyone else.  Even if he'd been brave enough to say it, he just didn't have the words yet.  When he woke up, neither of them talked about it, but Bobby greeted him with a glass of water and a couple of aspirin and they talked about servicing the Impala while he was here and that was almost as good.

But every once in a while, he thought about that pedicure and toyed with the idea of maybe, just maybe, telling Bobby the whole truth.

**Notes for the Chapter:**

> Disclaimer: My personal headcannon, based on what I observe in the show, is that Dean Winchester is genderqueer. However, I am not saying that he actually is, as that is something that cannot be decided by a third party, and I would only be convinced that he is canonically genderqueer if he said something on the show. I hope that my portrayal offends no one, since although a lot of it was taken from experiences of friends who are genderqueer, I myself am not. If you find something you disagree with, by all means let me know! I like to learn from my mistakes.


	3. Mary

**Summary for the Chapter:**

> "Mary got her first hint that Dean wasn't exactly normal when he was three years old."

**Notes for the Chapter:**

> Just a short and sweet fic to pass the time well I work on the more in-depth installments! Sorry for the long wait, school's been particularly crazy and I've been sick (though nothing life-threatening). :(
> 
> This is probably the last chapter in this particular fic (but no promises), and there will definitely be some more one-shots in the general series, so stay tuned! Also, I'm currently working on an AU of the genderqueer!verse where Mary survived the fire; an edited (happier) version of this may be the first chapter for that one as well.
> 
> So, I know John says that he and Mary had a perfect relationship, but evidence says otherwise. For one thing, in Dean's heaven, John is not living with Mary, and indeed they have an angry phone conversation at that point. Even on the night Mary died John was sleeping on the couch. They were basically held together by cupids long enough to produce the required two children and then left to fend for themselves.
> 
> Hope you guys enjoy!

Mary got her first hint that Dean wasn't exactly normal when he was three years old.  At the time, she didn't think much of it.  John was… well, it was one of the times when he wasn't living with her.  One of the times she'd hoped was a one time deal when it first happened, then a two time deal, then, well…  They say true love only exists in the movies, and her life sure wasn't on the silver screen.

So for now it was just her and her little angel.

She was just making lunch for him one afternoon when Dean came toddling up (he wasn't perfectly steady on his feet just yet) and tugged on her skirt.

"Mama," he said in his little baby voice that made her heart get warm.  Last time John had been by, he'd said that wasn't Dean a bit old for a lisp and shouldn't they start to teach him to talk like a 'big boy?'  She told him that Dean was three.  He'd countered back, she'd escalated…

And now she was alone again.

She wasn't even sure she wanted to be together anymore.

"Yes, angel?" she said, leaning down to meet his eyes with her warmest smile.  When she looked into her son's eyes, she remembered why she'd decided to leave hunting for good.  Why she had to protect this child.

"Why are your eyes pretty?"

Mary smiled.  "Your eyes are pretty too, Dean."

Dean made a frustrated face, the one that said he was trying to make himself understood but just didn't have the words yet.  "No, on the outside, with colors!"

Comprehension dawned on Mary.  "That's makeup, sweetheart.  I put it on in the morning so my eyes can be extra pretty," she said with a smile.  It was something she could do now that she couldn't before, something that reminded her she was out of the hunting life and her number one accessory didn't have to be a pistol.

"Make my eyes extra pretty," he demanded in the way of toddlers, and then paused.  "Please," he added as an afterthought.

Mary almost said no on impulse, because boys didn't _do_ that, but then thought better of it.  Why not?  He was just a kid, and anyways, it was flattering that her son wanted to be like her.  "Okay, since you asked nicely," she said, picking him up and balancing him on her hip, making a little 'oof.'  He was getting bigger by the day.  She took him to her room, setting up a couple of phone-books on the vanity chair and then boosting him up.  Her palate of eye-colors was already open on the counter.  "Welcome to Mommy's beauty salon," she joked, making Dean giggle.  "What color would you like today?"

"Puhple," Dean said, pointing at a pretty shade of lavender, close to what Mary was wearing that day.  She tried not to think to hard about what a 'girl' color that was, telling herself that Dean wouldn't want to spend this kind of time with her for long and to enjoy it.

"Alright, sweetheart," Mary said, taking up a small brush.  "Close your eyes."

Dean did so, squirming slightly but keeping his face mostly still.  Mary took his chin in her hand and gently brushed the lightest coat of purple over each eyelid, finishing with a kiss to his forehead before turning the chair so that he faced the mirror.  "All done, Dean, open your eyes!"

Mary had to work to restrain a laugh at the way Dean's mouth fell open.  He raised a finger to touch his eyelid, but Mary stopped him.  "Uh uh, you'll mess it up!"  _And get it all over your clothes_ , she silently added.

Dean obediently put his hand down.  "I'm pretty, Mommy!"

"Yes you are, honey," said Mary, pulling Dean into a hug.  "You sure are."

\--

Much to Mary's surprise, Dean's obsession with 'pretty' continued beyond that day.  The next time they were at Target, looking for new clothes (no one had prepared Mary for how quickly little boys grew) she sent Dean off for underwear and he came back with a pink package from the girl's section.

Thinking it was a mistake, Mary gently directed him back towards the boys' section, only to have Dean stamp his foot.  "These ones are pretty!" he said, sticking out his chin.

"Those ones are designed for girls," Mary explained quietly, trying not to attract attention.

Dean made a show of closely examining the boys' ones, before coming up with his answer.  "Same!" he said, obstinately sticking out his chin.

To tell the truth, Mary didn't really see the difference either.  Both were just strips of cotton that were used to cover a little kid's butt; both would wear out in less than a year.  "That's just the way it is, kiddo," she said regretfully.  She hated to have to introduce her son to something as shitty as human nature at such a young age.  Searching around for something to cheer him up, Mary's eyes landed on a little package of flower barrettes.  Dean's hair was a bit long; they could use these, and they would be easier to hide or explain away when John came back.  "How about this: you can have these if we get the plain white undies," she said.

The way Dean's face lit up as he nodded warmed her heart.  So what if her kid was growing up a little different?  At least he was growing up happy and safe, without a gun in his hand.  That was all she could ask for.

As soon as the check out lady had rung them through, Dean carried the bag with the barrettes, making his mom put them on him as soon as they got in the car, and to his credit, he worked them like nobody's business.

The barrettes had to go away in a couple of months when John made a reappearance at last, and with the excitement of a new person in the house Dean didn't even remember to miss them, so they remained at the back of Mary's makeup drawer until they burned in the fire.

**Notes for the Chapter:**

> Disclaimer: My personal headcannon, based on what I observe in the show, is that Dean Winchester is genderqueer. However, I am not saying that he actually is, as that is something that cannot be decided by a third party, and I would only be convinced that he is canonically genderqueer if he said something on the show. I hope that my portrayal offends no one, since although a lot of it was taken from experiences of friends who are genderqueer, I myself am not. If you find something you disagree with, by all means let me know! I like to learn from my mistakes.


End file.
